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Is there a speaker dock that can:
work with both the iPod Touch and iPad
work with an iPad inside an Otterbox Defender
work with an iPod inside an Otterbox Defender

I'd thought the adjustability of the iLuv imm747 might work, but have read numerous reviews stating that it works only with the slimmest of cases.

Likewise, many of the other speaker docks that function with both devices rarely state whether they can work with the device while it is inside a case, nor do their technical specs include measurements for the docking area.

I dont know of any speaker dock that work with these cases. You want to consider a dock extender type cable. It has a male 30 pin on one end and a female 30 pin on the other. A place like cablejive carries them.